Substituted O-alkylsulfonylglycolic acid anilides

ABSTRACT

New and valuable O-substituted glycolic acid anilides having a good herbicidal action, a process for their manufacture, herbicides containing these new compounds as active ingredients, and a process for controlling the growth of unwanted plants with these active ingredients.

This is a division, of application Ser. No. 638,957 filed Dec. 8, 1975now abandoned.

The present invention relates to new and valuable O-substituted glycolicacid anilides having a good herbicidal action, a process for theirmanufacture, herbicides containing these new compounds as activeingredients, and a process for selective weed control in crops with thenew active ingredients or agents containing them.

It is known (German Laid-Open Application DOS No. 2,160,380) to useO-alkylsulfonylglycolic acid anilides, particularlyO-methylsulfonylglycolic acid-(N-sec-butyl)-anilide, as herbicides.However, their herbicidal action is poor.

It is an object of the present invention to provide O-substitutedglycolic acid anilides having superior plant-influencing properties andwhich at low application rates combat a larger number of weed species,and particularly very resistant weeds, much better than the prior artO-substituted glycolic acid anilides without causing damage to cropplants.

We have found that substituted O-alkylsulfonylglycolic acid anilides ofthe formula ##STR1## where R¹ denotes hydrogen, methyl, ethyl. n-propylor isopropyl, R² denotes methyl, ethyl, n-propyl or isopropyl, R³denotes alkyl of a maximum of 3 carbon atoms, alkenyl of 3 or 4 carbonatoms, cyclopropyl or cyclopropylmethyl, Y denotes an unsubstitutedethylene chain (--CH₂ --CH₂ --) or an ethylene chain monosubstituted byethyl or having one or two methyl substituents, and R⁴ denotes lower,optionally halogen-substituted, alkyl of a maximum of 4 carbon atoms(methyl, ethyl, chloroethyl, chloromethyl, propyl, isopropyl, butyl,isobutyl, sec-butyl), have a better herbidical action than the prior artcompounds.

The superior action of the new O-substituted glycolic acid anilidesaccording to the invention is atttibutable to the fact that theirchemical structure deviates basically from that of the prior artcompounds.

The new O-substituted glycolic acid anilides of the formula I areprepared in accordance with the invention by reacting an N-substitutedglycolic acid anilide of the formula ##STR2## with a sulfonyl halide ofthe formula ##STR3## in the presence of an acid-binding agent. Informulae II and III, R¹, R², R³, Y and R⁴ have the meanings given atformula I. Hal denotes a halogen atom.

The reaction may be carried out in the presence or absence of solventsor diluents which are inert to the reactants, e.g., aliphatic, aromaticor halogenated hydrocarbons, such as benzene, toluene, xylenes,petroleum ether, chlorobenzene, methylene chloride, 1,2-dichloroethaneand chloroform; ethers and ethereal compounds, such as dialkyl ether,dioxane and tetrahydrofuran; nitriles, such as acetonitrile;N,N-dialkylated amides, such as dimethylformamide, and mixtures of thesesolvents.

Preferred sulfonyl halides are the acid chlorides of methanesulfonicacid, ethanesulfonic acid, propanesulfonic acid, isopropanesulfonicacid, chloromethanesulfonic acid and chloroethanesulfonic acid.

The reaction is carried out at a temperature of from -30° to +100° C.,preferably from -5° to +30° C., in the presence of an acid-bindingagent. Suitable acid-binding agents are tertiary amines, such astrialkylamines, e.g., triethylamine, pyridine and pyridine bases, andinorganic bases, such as the oxides, hydroxides, hydrogen carbonates andcarbonates of alkali and alkaline earth metals.

The starting materials of the formula II are new; they may be preparedby known methods, e.g., by reaction of N-substituted anilines of theformula ##STR4## with acetoxyacetyl chloride to give the correspondingacetoxyacetanilide of the formula ##STR5## followed by elimination ofthe acyl radical by hydrolysis or transesterification to give a glycolicacid anilide of the formula ##STR6##

The starting materials of the formula IV are known, e.g., from GermanLaid-Open Applications DOS No. 2,305,495 and DOS No. 2,328,340.

Some of the compounds according to the invention of the formula I may beprepared in a single stage process by reaction of N-substituted anilinesof the formula IV with an O-substituted glycolic acid halide of theformula ##STR7## in the presence of an acid-binding agent; R⁵ denotesalkyl, especially methyl and ethyl. Starting materials of the formulaVII are disclosed in U.S. Pat. No. 3,200,138.

The preparation of the compounds of the invention is illustrated by thefollowing examples.

EXAMPLE 1 (a) 2,6-dimethyl-N-1-(methoxyprop-2-yl)-acetoxyacetanilide

At 0° to +5° C. and while stirring, a mixture of 152 parts by weight of2,6-dimethyl-N-(1-methoxyprop-2-yl)-aniline, 79.5 parts by weight oftriethylamine and 220 parts by weight of toluene was added at a ratedepending on the heat of reaction to a solution of 107.5 parts by weightof acetoxyacetyl chloride in 500 parts by weight of toluene. When thereaction was over, the mixture was extracted with water, dilutehydrochloric acid and dilute sodium bicarbonate solution. The organicphase was dried with magnesium sulfate and freed from solvent in vacuo.The crude product obtained was used without further purification in thefollowing reaction.

(b) 2,6-dimethyl-N-(1-methoxypro-2-yl)-glycolic acid anilide

183 parts by weight of the crude2,6-dimethyl-N-(1-methoxyprop-2-yl)-acetoxyacetanilide was dissolved ina mixture of 240 parts by weight of water and 800 parts by weight ofmethanol; the whole was then hydrolyzed at 40° to 45° C. by the additionof a solution of 36.6 parts by weight of potassium hydroxide in 310parts by weight of methanol.

The reaction mixture was worked up by substantially freeing it fromsolvent and extracting the reaction product with dichloromethane.

Upon concentration of the dried dichloromethane solution a crystallinecrude product was obtained which was further purified byrecrystallization from diethyl ether; m.p.: 77° to 78° C.

The compound has the following structural formula: ##STR8##

(c) 2,6-dimethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonyloxyglycolic acidanilide

At 0° to +5° C. a solution of 13.7 parts by weight of methanesulfochloride in 26 parts by weight of dichloromethane was added to asolution of 25.1 parts by weight of2,6-dimethyl-N-(1-methoxyprop-2-yl)-glycolic acid anilide and 13.2 partsby weight of triethylamine in 130 parts by weight of dichloromethane.The reaction mixture was worked up by treatment with water, dilutehydrochloric acid and dilute sodium bicarbonate solution. Thedichloromethane solution was dried with magnesium sulfate andconcentrated, the crude product being obtained as crystals. Afterrecrystallization from diisopropyl ether the analytically pure substancemelts at 77° C.

The compound has the following structural formula: ##STR9##

EXAMPLE 2 2-methyl-6-ethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonyloxyglycolic acid anilide

At 0° to +5° C. a solution of 207 parts by weight of2-methyl-6-ethyl-N-(1-methoxyprop-2-yl)-aniline and 122 parts by weightof triethylamine in 450 parts by weight of tetrahydrofuran was added toa solution of 190 parts by weight of O-methylsulfonylglycolic acidchloride in 450 parts by weight of tetrahydrofuran. The mixture wasafterreacted for 1 hour by stirring it at room temperature (20° C.).Subsequently the hydrochloride was separated and the filtrateconcentrated in vacuo. The oily residue was dissolved in ethyl acetateand extracted with water, dilute hydrochloric acid and dilute sodiumbicarbonate solution. The organic phase was dried with magnesiumsulfate, treated with activated carbon and silica gel, and subsequentlyconcentrated in vacuo.

The oil which remained (n_(D) ²⁵ : 1.5170) did not crystallize out evenafter standing for a fairly long period of time.

The spectroscopic data and the ultimate analysis results agree with thefollowing structure: ##STR10##

The following compounds were prepared in accordance with the proceduredescribed in the foregoing examples:

    __________________________________________________________________________     ##STR11##                                                                    R.sup.2                                                                            R.sup.1                                                                          Y         R.sup.3  R.sup.4                                            __________________________________________________________________________    CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.2 H.sub.5                                                                    n.sub. D.sup. 25 1.5161                       CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.2 H.sub.5                                                                    n.sub. D.sup. 25 1.5120                       CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.3 H.sub.7                                    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.3 H.sub.7                                                                    n .sub.D.sup.25 1.5110                        CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 i-C.sub.3 H.sub.7                                  CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 i-C.sub.3 H.sub.7                                                                  n.sub. D.sup. 25  1.5110                      C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.3                                                                           n.sub. D.sup. 18 1.5189                       C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.2 H.sub.5                                    C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.3 H.sub.7                                    C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 i-C.sub.3 H.sub.7                                  CH.sub.3                                                                           H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.3                                           CH.sub.3                                                                           H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.2 H.sub.5                                    CH.sub.3                                                                           H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.3 H.sub.7                                    CH.sub.3                                                                           H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 i-C.sub.3 H.sub.7                                  C.sub.2 H.sub.5                                                                    H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.3                                                                           n.sub. D.sup. 25 1.5170                       C.sub.2 H.sub.5                                                                    H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 C.sub.2 H.sub.5                                                                    n.sub. D.sup. 25 1.5140                       C.sub.2 H.sub.5                                                                    H  CH(CH.sub. 3)CH.sub.2                                                                   CH.sub.3 C.sub.3 H.sub.7                                    C.sub.2 H.sub.5                                                                    H  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 i-C.sub.3 H.sub.7                                  CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                           CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                                                           n.sub. D.sup..sup.25 1.5185                   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.2 CH.sub.2                                                                       C.sub.2 H.sub.5                                                                        CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.2 CH.sub.2                                                                       i-C.sub.3 H.sub.7                                                                      CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.2 CH.sub.2                                                                       CH.sub.2 CHCH.sub.2                                                                    CH.sub.3                                           CH.sub.3                                                                           H  CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                           i-C.sub.3 H.sub.7                                                                  H  CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                           C.sub.2 H.sub.5                                                                    H  CH.sub.2 CH.sub.2                                                                       CH.sub.3 CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    C.sub.2 H.sub.5                                                                        CH.sub.3                                           CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH(CH.sub. 3)CH.sub.2                                                                   C.sub.2 H.sub.5                                                                        CH.sub.3                                           C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    C.sub.2 H.sub.5                                                                        CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.2 CH(CH.sub.3)                                                                   CH.sub.3 CH.sub.3                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                         CH.sub.2 CH(CH.sub.3)                                                                   CH.sub.3 CH.sub.3                                           C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH.sub.2 CH(CH.sub.3)                                                                   CH.sub.3 CH.sub.3                                           CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.2 Cl                                        CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.2 Cl                                        C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    CH.sub.3 CH.sub.2 Cl                                        CH.sub.3                                                                           CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    C.sub.2 H.sub.5                                                                        CH.sub.2 Cl                                        C.sub.2 H.sub.5                                                                    CH.sub.3                                                                         CH(CH.sub.3)CH.sub.2                                                                    C.sub.2 H.sub.5                                                                        CH.sub.2 Cl                                        C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                  CH(CH.sub.3)CH.sub.2                                                                    C.sub.3 H.sub.7                                                                        CH.sub.2 Cl                                        CH.sub.3                                                                           C.sub.2 H.sub.5                                                                  CH.sub.2CH.sub.2                                                                        CH.sub.3 C.sub.2 H.sub.5                                                                    n.sub. D.sup. 25 1.5135                       __________________________________________________________________________

Application may be effected for instance in the form of directlysprayable solutions, powders, suspensions, dispersions, emulsions, oildispersions, pastes, dusts, broadcasting agents, or granules byspraying, atomizing, dusting, broadcasting or watering. The forms ofapplication depend entirely on the purpose for which the agents arebeing used; in any case they should ensure a fine distribution of theactive ingredient.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, etc. andoils of vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,etc., and strongly polar solvents such as dimethyl-formamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,oil dispersions or wettable powders by adding water. To prepareemulsions, pastes and oil dispersions the ingredients as such ordissolved in an oil or solvent may be homogenized in water by means ofwetting or dispersing agents, adherents or emulsifiers. Concentrateswhich are suitable for dilution with water may be prepared from activeingredient, wetting agent, adherent, emulsifying or dispersing agent andpossibly solvent or oil.

Examples of surfactants are: alkyli metal, alkaline earth metal andammonium salts of ligninsulfonic acid, naphthalene-sulfonic acids,phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkylsulfonates, alkali metal and alkaline earth metal salts ofdibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcoholsulfates, alkali metal and alkaline earth metal salts of fatty acids,salts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof sulfated fatty alcohol glycol ether, condensation products ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensation products of naphthalene or naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers,alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol ester, lignin, sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silica gel, silicic acid,silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground plastics, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, andvegetable products such as grain flours, bark meal, wood meal, andnutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90% byweight of active ingredient.

There may be added to the compositions or individual active ingredients(if desired, immediately before use (tank-mix) oils of various types,herbicides, fungicides, nematocides, insecticides, bactericides, traceelements, fertilizers, antifoams (e.g., silicones), growth regulators,antidotes and other herbicidally effective compounds such as

substituted anilines

substituted aryloxycarboxylic acids and salts, esters and amidesthereof,

substituted ethers

substituted arsonic acids and their salts, esters and amides

substituted benzimidazoles

substituted benzisothiazoles

substituted benzothiadiazinone dioxides

substituted benzoxazines

substituted benzoxazinones

substituted benzothiadiazoles

substituted biurets

substituted quinolines

substituted carbamates

substituted aliphatic carboxylic acids and their salts, esters andamides

substituted aromatic carboxylic acids and their salts, esters and amides

substituted carbamoylalkylthiol- or -dithiophosphates

substituted quinazolines

substituted cycloalkylamidocarbothiolic acids and their salts, estersand amides

substituted cycloalkylcarbonamidothiazoles

substituted dicarboxylic acids and their salts, esters and amides

substituted dihydrobenzofuranyl sulfonates

substituted disulfides

substituted dipyridylium salts

substituted dithiocarbamates

substituted dithiophosphoric acids and their salts, esters and amides

substituted ureas

substituted hexahydro-1H-carbothioates

substituted hydantoins

substituted hydrazides

substituted hydrazonium salts

substituted isoxazole pyrimidones

substituted imidazoles

substituted isothiazole pyrimidones

substituted ketones

substituted naphthoquinones

substituted aliphatic nitriles

substituted aromatic nitriles

substituted oxadiazoles

substituted oxadiazinones

substituted oxadiazolidine diones

substituted oxadiazine diones

substituted phenols and their salts and esters

substituted phosphonic acids and their salts, esters and amides

substituted phosphonium chlorides

substituted phosphonalkyl glycines

substituted phosphites

substituted phosphoric acids and their salts, esters and amides

substituted piperidines

substituted pyrazoles

substituted pyrazole alkylcarboxylic acids and their salts, esters andamides

substituted pyrazolium salts

substituted pyrazolium alkyl sulfates

substituted pyridazines

substituted pyridazones

substituted pyridine carboxylic acids and their salts, esters and amides

substituted pyridines

substituted pyridine carboxylates

substituted pyridinones

substituted pyrimidines

substituted pyrimidones

substituted pyrrolidine carboxylic acid and its salts, esters and amides

substituted pyrrolidines

substituted pyrrolidones

substituted arylsulfonic acids and their salts, esters and amides

substituted styrenes

substituted tetrahydrooxadiazine diones

substituted tetrahydroxadiazole diones

substituted tetrahydromethanoindenes

substituted tetrahydroxadiazole thiones

substituted tetrahydrothiadiazine thiones

substituted tetrahydrothiadiazole diones

substituted aromatic thiocarbonylamides

substituted thiocarboxylic acids and their salts, esters and amides

substituted thiol carbamates

substituted thioureas

substituted thiophosphoric acids and their salts, esters and amides

substituted triazines

substituted triazoles

substituted uracils, and

substituted uretidine diones.

The last-mentioned herbicidal compounds may also be applied before orafter the active ingredients or compositions thereof according to theinvention.

These agents may be added to the herbicides according to the inventionin a ratio by weight of from 1:10 to 10:1. The same applies to oils,fungicides, nematocides, insecticides, bactericides, antidotes andgrowth regulators.

The amount used of the agents according to the invention may vary anddepends in essence on the type of effect to be achieved; it is generallyfrom 0.1 to 15 (and more), preferably from 0.2 to 6, kg per hectare ofactive ingredient. The agents according to the invention may be usedonce or several times before or after planting, before sowing, andbefore, during or after emergence of the crop plants and unwantedplants.

The new compositions have a strong herbicidal action and may thereforebe used as weedkillers or for controlling the growth of unwanted plants.Whether the new active ingredients are used as total or selective agentsdepends in essence on the amount of ingredient used per unit area.

By weeds and unwanted plant growth are meant all monocotyledonous anddicotyledonous plants which grow in loci where they are not desired.

The agents according to the invention may therefore be used forcontrolling for instance

    ______________________________________                                        Gramineae, such as                                                             Cynodon spp.       Dactylis spp.                                              Digitaria spp.     Avena spp.                                                 Echinochloa spp.   Bromus spp.                                                Setaria spp.       Uniola spp.                                                Panicum spp.       Poa spp.                                                   Alopecurus spp.    Leptochloa spp.                                            Lolium spp.        Brachiaria spp.                                            Sorghum spp.       Eleusine spp.                                              Agropyron spp.     Cenchrus spp.                                              Phalaris spp.      Eragrostis spp.                                            Apera spp.         Phragmites communis                                        etc.;                                                                        Cyperaceae, such as                                                            Carex spp.         Eleocharis spp.                                            Cyperus spp.       Scirpus spp.                                               etc.;                                                                        dicotyledonous weeds, such as                                                 Malvaceae, e.g.,                                                               Abutilon theoprasti                                                                              Hibiscus spp.                                              Sida spp.          Malva spp.                                                 etc.;                                                                        Compositae, such as                                                            Ambrosia spp.      Centaurea spp.                                             Lactuca spp.       Tussilago spp.                                             Senecio spp.       Lapsana communis                                           Sonchus spp.       Tagetes spp.                                               Xanthium spp.      Erigeron spp.                                              Iva spp.           Anthemis spp.                                              Galinsoga spp.     Matricaria spp.                                            Taraxacum spp.     Artemisia spp.                                             Chrysanthemum spp. Bidens spp.                                                Cirsium spp.       etc.;                                                     Convolvulaceae, such as                                                        Convolvulus spp.   Cuscuta spp.                                               Ipomoea spp.       Jaquemontia tamnifolia                                     etc.;                                                                        Cruciferae, such as                                                            Barbarea vulgaris  Arabidopsis thaliana                                       Brassica spp.      Descurainia spp.                                           Capsella spp.      Draba spp.                                                 Sisymbrium spp.    Coronopus didymus                                          Thlaspi spp.       Lepidium spp.                                              Sinapis arvensis   Raphanus spp.                                              etc.;                                                                        Geraniaceae, such as                                                           Erodium spp.       Geranium spp.                                              etc.;                                                                        Portulacaceae, such as                                                         Portulaca spp.     etc.;                                                     Primulaceae, such as                                                           Anagallis arvensis Lysimachia spp.                                            etc.;                                                                        Rubiaceae, such as                                                             Richardia spp.     Diodia spp.                                                Galium spp.        etc.;                                                     Scrophulariaceae, such as                                                      Linaria spp.       Digitalis spp.                                             Veronica spp.      etc.;                                                     Solanaceae, such as                                                            Physalis spp.      Nicandra spp.                                              Solanum spp.       Datura spp.                                                etc.;                                                                        Urticaceae, such as                                                            Urtica spp.                                                                  Violaceae, such as                                                             Viola spp.         etc.;                                                     Zygophyllaceae, such as                                                        Tribulus terrestris                                                                              etc.;                                                     Euphorbiaceae, such as                                                         Mercurialis annua  Euphorbia spp.                                            Umbelliferae, such as                                                          Daucus carota      Ammi majus                                                 Aethusa cynapium   etc.;                                                     Commelinaceae, such as                                                         Commelina spp.     etc.;                                                     Labiatae, such as                                                              Lamium spp.        Galeopsis spp.                                             etc.;                                                                        Leguminosae, such as                                                           Medicago spp.      Sesbania exaltata                                          Trifolium spp.     Cassia spp.                                                Vicia spp.         Lathyrus spp.                                              etc.;                                                                        Plantaginaceae, such as                                                        Plantago spp.      etc.;                                                     Polygonaceae, such as                                                          Polygonum spp.     Fagopyrum spp.                                             Rumex spp.         etc.;                                                     Aizoaceae, such as                                                             Mollugo verticillata                                                                             etc.;                                                     Amaranthaceae, such as                                                         Amaranthus spp.    etc.;                                                     Boraginaceae, such as                                                          Amsinckia spp.     Anchusa spp.                                                Myostis spp.      Lithospermum spp.                                          etc.;                                                                        Caryophyllaceae, such as                                                       Stellaria spp.     Silene spp.                                                Spergula spp.      Cerastium spp.                                             Saponaria spp.     Agrostemma githago                                         Scleranthus annuus etc.;                                                     Chenopodiaceae, such as                                                        Chenopodium spp.   Atriplex spp.                                              Kochia spp.        Monolepsis nuttalliana                                     Salsola Kali       etc.;                                                     Lythraceae, such as                                                            Cuphea spp.        etc.;                                                     Oxalidaceae, such as                                                           Oxalis spp.                                                                  Ranunculaceae, such as                                                         Ranunculus spp.    Adonis spp.                                                Delphinium spp.    etc.;                                                     Papaveraceae, such as                                                          Papaver spp.       Fumaria offinicalis                                        etc.;                                                                        Onagraceae, such as                                                            Jussiaea spp.      etc.;                                                     Rosaceae, such as                                                              Alchemillia spp.   Potentilla spp.                                            etc.;                                                                        Potamogetonaceae, such as                                                      Potamogeton spp.   etc.;                                                     Najadaceae, such as                                                            Najas spp.         etc.;                                                     Equisetaceae                                                                   Equisetum spp.     etc.;                                                     Marsileaceae, such as                                                          Marsilea quadrifolia                                                                             etc.;                                                     Polypodiaceae,                                                                 Pteridium quilinum                                                           Alismataceae, such as                                                          Alisma spp.        Sagittaria sagittifolia                                    etc.;                                                                        The herbicides according to the invention may be employed                     in cereal crops such as                                                        Avena spp.         Sorghum                                                    Triticum spp.      Zea mays                                                   Hordeum spp.       Panicum miliaceum                                          Secale spp.        Oryza spp.                                                 Saccharum offinicarum                                                        and in dicotyledon crops such as                                              Crucifereae, e.g.                                                              Brassica spp.      Raphanus spp.                                               Sinapis spp.      Lepidium spp.                                             Compositae, e.g.                                                               Lactuca spp.       Carthamus spp.                                             Helianthus spp.    Scorzonera spp.                                           Malvaceae, e.g.                                                                Gossypium hirsutum                                                           Leguminesae, e.g.                                                              Medicago spp.      Phaseolus spp.                                             Trifolium spp.     Arachis spp.                                               Pisum spp.         Glycine max.                                              Chenopodiaceae, e.g.                                                           Beta vulgaris                                                                 Spinacia spp.                                                                Solanaceae, e.g.                                                               Solanum spp.       Capsicum annuum                                            Nicotiania spp.                                                              Linaceae, e.g.                                                                 Linum spp.                                                                   Umbelliferae, e.g.                                                             Petroselinum spp.  Apium graveolens                                           Daucus carota                                                                Rosaceae, e.g.      Fragaria                                                  Cucurbitaceae, e.g.                                                            Cucumis spp.       Cucurbita spp.                                            Liliaceae, e.g.                                                                Allium spp.                                                                  Vitaceae, e.g.                                                                 Vitis vinifera                                                               Bromeliaceae, e.g.                                                             Ananas sativus.                                                              ______________________________________                                    

EXAMPLE 3

In the greenhouse, loamy sandy soil was filled into pots and sown withthe seeds of various plants. The soil was then immediately treated with0.8 kg/ha of each of the following active ingredients, each beingdispersed or emulsified in 500 liters of water per hectare:

I 2,6-diethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonylglycolic acidanilide

II 2,6-dimethyl-N-(1-methoxyprop-2-yl)-O-ethylsulfonylglycolic acidanilide

III 2,6-dimethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonylglycolic acidanilide

and for comparison,

IV O-methylsulfonylglycolic acid-N-sec-butylanilide

After 4 to 5 weeks it was ascertained that active ingredients I, II andIII had a better herbicidal action than compound IV, combined with thesame crop tolerance.

The results are given below:

    ______________________________________                                        Active ingredient                                                                            I        II       III    IV                                    kg/na          0.8      0.8      0.8    0.8                                   ______________________________________                                        Crop plants:                                                                  Gossypium hirsutum                                                                           0        0        0      0                                     Zea mays       0        0        0      0                                     Glycine max.   0        0        0      0                                     Oryza sativa   0        0        0      0                                     Brassica spp.  0        0        0      0                                     Beta vulgaris  0        0        0      0                                     Unwanted plants:                                                              Echinochloa crus-galli                                                                       75       85       90     30                                    Digitaria sanguinalis                                                                        80       90       80     60                                    ______________________________________                                         0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 4

In the greenhouse, various plants were treated at a growth height offrom 2 to 18 cm with 0.8 kg/ha of each of active ingredients I, II andIII and comparative agent IV, each being dispersed or emulsified in 500liters of water per hectare.

After 2 to 3 weeks it was ascertained that active ingredients I, II andII provided better weed control than IV, combined with the same cropplant compatibility.

The results are given below:

    ______________________________________                                        Active ingredient                                                                            I        II       III    IV                                    kg/ha          0.8      0.8      0.8    0.8                                   ______________________________________                                        Crop plants:                                                                  Gossypium hirsutum                                                                           0        0        0      0                                     Zea mays       0        0        0      0                                     Glycine max.   0        0        0      0                                     Brassica spp.  10       10       10     0                                     Unwanted plants                                                               Echinochloa crus-galli                                                                       80       95       90     30                                    ______________________________________                                         0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 5

In the greenhouse, loamy sandy soil was filled into pots and sown withthe seeds of various plants. The soil was then immediately treated with3 kg/ha of each of the following active ingredients, each beingdispersed or emulsified in 500 liters of water per hectare:

I. 2,6-diethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonylglycolic acidanilide

II. 2,6-dimethyl-N-(1-methoxyprop-2-yl)-O-ethylsulfonylglycolic acidanilide

III. 2,6-dimethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonylglycolic acidanilide

V. 2-methyl-6-ethyl-N-(1-methoxyprop-2-yl)-O-ethylsulfonylglycolic acidanilide

VI. 2-methyl-6-ethyl-N-(1-methoxyprop-2-yl)-O-isopropylsulfonylglycolicacid anilide

VII. 2-methyl-6-ethyl-N-(1-methoxyprop-2-yl)-O-methylsulfonylglycolicacid anilide.

After 4 to 5 weeks it was ascertained that the active ingredients had astrong herbicidal action and were well tolerated by the crop plants.

The results are given below:

    ______________________________________                                        Active ingredient                                                                            I      II     III  V    VI   VII                               kg/ha          3      3      3    3    3    3                                 ______________________________________                                        Crop plants:                                                                  Gossypium hirsutum                                                                           10     10     0    0    0    0                                 Glycine max.   0      0      0    0    0    0                                 Zea mays       0      0      0    0    0    0                                 Unwanted plants                                                               Echinochloa crus-galli                                                                       100    100    100  100  100  100                               Lolium multiflorum                                                                           100    100    100  100  100  100                               ______________________________________                                         0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 6

In the greenhouse, various plants were treated at a growth height offrom 2 to 18 cm with 3 kg/ha of each of active ingredients I, II, III,V, VI and VII, each being dispersed or emulsified in 500 liters of waterper hectare.

After 2 to 3 weeks it was ascertained that the active ingredients had astrong herbicidal action and were well tolerated by the crop plants.

The results are given below:

    ______________________________________                                        Active ingredient                                                                            I      II     III  V    VI   VII                               kg/ha          3      3      3    3    3    3                                 ______________________________________                                        Crop plants:                                                                  Gossypium hirsutum                                                                           0      0      0    0    0    0                                 Zea mays       0      0      0    0    0    0                                 Glycine max.   0      0      0    0    0    0                                 Unwanted plants:                                                              Echinochloa crus-galli                                                                       100    90     70   90   95   100                               Lolium multiflorum                                                                            80    90     80   90   85   100                               ______________________________________                                         0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 7

90 parts by weight of compound I is mixed with 10 parts by weight ofN-methyl-α-pyrrolidone. A mixture is obtained which is suitable forapplication in the form of very fine drops.

EXAMPLE 8

20 parts by weight of compound II is dissolved in a mixture consistingof 80 parts by weight of xylene, 10 parts by weight of the adduct of 8to 10 moles of ethylene oxide to 1 mole of oleicacid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide to 1 mole of castor oil. By pouring the solutioninto 100,000 parts by weight of water and uniformly distributing ittherein, an aqueous dispersion is obtained containing 0.02% by weight ofthe active ingredient.

EXAMPLE 9

20 parts by weight of compound III is dissolved in a mixture consistingof 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 moles of ethyleneoxide to 1 mole of isooctylphenol, and 10 parts by weight of the adductof 40 moles of ethylene oxide to 1 mole of castor oil. By pouring thesolution into 100,000 parts by weight of water and uniformlydistributing it therein, an aqueous dispersion is obtained containing0.02% by weight of the active ingredient.

EXAMPLE 10

20 parts by weight of compound I is dissolved in a mixture consisting of25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210° and 280° C., and 10 partsby weight of the adduct of 40 moles of ethylene oxide to 1 mole ofcastor oil. By pouring the solution into 100,000 parts by weight ofwater and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

EXAMPLE 11

20 parts by weight of compound I is well mixed with 3 parts by weight ofthe sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts byweight of the sodium salt of a ligninsulfonic acid obtained from asulfite waste liquor, and 60 parts by weight of powdered silica gel, andtriturated in a hammer mill. By uniformly distributing the mixture in20,000 parts by weight of water, a spray liquid is obtained containing0.1% by weight of the active ingredient.

EXAMPLE 12

3 parts by weight of compound II is intimately mixed with 97 parts byweight of particulate kaolin. A dust is obtained containing 3% by weightof the active ingredient.

EXAMPLE 13

30 parts by weight of compound II is intimately mixed with a mixtureconsisting of 92 parts by weight of powdered silica gel and 8 parts byweight of paraffin oil which has been sprayed onto the surface of thissilica gel. A formulation of the active ingredient is obtained havinggood adherence.

EXAMPLE 14

In the greenhouse the compounds ##STR12## were compared in the followingexperiments. Various crop plants and unwanted grasses were sown,separated by species, into pots filled with loamy sand soil. The soilwas then immediately treated with the active ingredients, each beingdispersed or emulsified in 500 liters of water per hectare. During theexperiment the pots were kept thoroughly moist.

The individual plant species, the amounts of active ingredient and theiraction are apparent from the following table.

It was ascertained that the action of I is similar to that of II onunwanted grasses. The selectivity of I is however far better than thatof II in cereals. As no damage is caused to white mustard, activeingredient I may be used in broad-leaved crops.

    ______________________________________                                        Active ingredient                                                                        I               II (prior art)                                     kg/ha      0.5    1.0    2.0  3.0  0.5 1.0 2.0  3.0                           ______________________________________                                        Avena sativa (oats)                                                                      --     --     --   0    --  57  67   --                            Triticum aestivum                                                             (wheat)    0      0      0    30   36  54  74   68                            Sinapis alba                                                                  (white mustard)                                                                          0      0      0    --   25  45  60   70                            Alopecurus                                                                    myosuroides                                                                              40     40     80   --   65  85  95   --                            Echinochloa                                                                   crus-galli 100    100    100  100  89  99  100  100                           Lolium                                                                        multiflorum                                                                              --     --     --   100  83  98  100  --                            ______________________________________                                         0 = no damage                                                                 100 = complete destruction                                               

We claim:
 1. A substituted O-alkylsulfonylglycolic acid anilide of theformula ##STR13## where R¹ denotes methyl or ethyl, R² denotes methyl,ethyl, or isopropyl, R³ denotes methyl, ethyl, isopropyl or --CH₂CH═CH₂, Y denotes --CH₂ CH₂ --, and R⁴ denotes methyl or ethyl.
 2. Asubstituted O-alkylsulfonylglycolic acid anilide as claimed in claim 1wherein R³ is methyl and each of R¹, R² and R⁴ is methyl or ethyl.
 3. Asubstituted O-alkylsulfonylglycolic acid anilide as claimed in claim 1wherein R³ is methyl and each of R¹, R² and R⁴ is methyl.
 4. Asubstituted O-alkylsulfonylglycolic acid anilide as claimed in claim 1wherein R³ is methyl, R¹ is ethyl and R² and R⁴ are methyl.
 5. Asubstituted O-alkylsulfonylglycolic acid anilide as claimed in claim 1wherein R³ is methyl, R¹ and R² are each ethyl, and R⁴ is methyl.
 6. Asubstituted O-alkylsulfonylglycolic acid anilide as claimed in claim 1wherein R³ is methyl, R¹ and R⁴ are each ethyl, and R² is methyl.